My Vacation Methodology

(Updated May 31, 2023)

“If you fail to plan, you are planning to fail!” — Benjamin Franklin

When it comes to my travels, I take Ben’s words to heart.

Many friends and co-workers are mesmerized by my travel exploits. Some believe I’m wealthy; others believe I found that pot of gold at the end of the rainbow. Neither belief is true. My ability to travel is nothing more than the result of proper travel planning.

As I prepared to embark on Adventure 2018: Summer Edition, I thought this is a great time to discuss my vacation methodology. Hopefully, it will inspire others.

The very first thing I do is narrow down my vacation location choices. Shocking, I know. For many people, deciding to take a vacation it the toughest decision.

It was for me too, until March 8, 2013.

Actually selecting a vacation destination is the easiest part of my planning. In 2015, I sat down and made a list of the places I wanted to visit over the next ten years, each with a different theme:

2015 Land of Hope & Glory
2016 Pure Tourist:
2017 Hidden Gems:
Lancaster & Blackpool
2018 Why Not:
Londonium Weekend
2019 Because I Want Too:
Birthday Extravaganza 2019
French Riviera: Dream Come True
Parisian Pitsop
Tea with the Queen
“Bear and the Strawberry Tree”
Brussels: The Unofficial Capital of Europe

In Bruges
2020 Crown of Central Europe – rescheduled due to COVID-19 pandemic
2021 Welcome Back to the World:
Amsterdam Adventures
Barcelona Getaway
Berlin Weekend
Visiting “The Rock” … of Gibraltar
Aventuras En Málaga 
Vienna Adventures
‘K’nightime in Bruges
Chillin in Paris
2022 Happy Return to Adventure:
Happy Easter from Bath
Munich Layover
Prague: Golden City of a Thousand Spires
Venice: The Floating City
The Islands of the Venice Lagoon
Porto: The Invicta City
Lisbon: The City of Spies
Hamburg: Gateway to the World
Crete: Island of Heroes
Exploring Crete in a Jeep
2023 Adventure in Nordic and and Swiss Country:
Stumbling through Köln
Strolling through København
2024 Romance in the Air: Northern Italy with Venice & Tuscany
2025 Classic Germany, Switzerland & Austria

Yes, there are a lot of European cities on this list. No, it doesn’t mean I’m avoiding other areas of the world. I have those areas listed as well:

2027Japan, Then & Now
2029Wonders of New Zealand & Australia
2031Golden Triangle of India

Of course this list is subject to change due to a variety of factors including world situations, governmental restrictions, financial, and most importantly – desire.

Wow, even as I type this, I shock myself with how OCD I am about my vacations. Then again, according to the True Colors Personality Test, I’m a Gold/Green (or Green/Gold on Tuesdays and Fridays, lol). As such I tend to be a little compulsive when it comes to organizing and planning. As you will read, this trait spills over into my vacation planning as well.

Random thought: many of my friends have Orange personalities, which equates to a more carpe diem lifestyle – except of course when it comes to taking a vacation. Funny, huh?


Research can be very fun, if not strenuous and nerve wrecking. I found this to be true when researching and comparing flights. There are so many travel sites out there with loads of information on when to buy airline tickets; when not to buy a ticket; what airline is the best; which airline sucks; what time to fly, and so on.

The key thing I learned from all the info on these sites is this: it is not an exact science and every site is based on individual opinions and experiences; and not everyone’s experiences are going to be the same.

Best advice? Set up a price tracker to track prices. I’ve used Google Flights, but there are others like Skyscanner, Airfarewatchdog and Hopper.

There was one thing I read on travel sites that I agreed with – when you find the flight that meets your needs and wants, book your ticket – don’t wait. However, make sure to read the fine print.

Many airlines now offer a Basic Economy option, meaning all you get is a seat on the plane. No frills, no thrills, and you can’t even bring a carry-on or select your seat. I love reading the negative comments about how Spirit Airlines nickels and dimes every bit of their travel. Seriously, did you really think you’re get first-class treatment for $100? Haha, good one!

Take a moment and read Katherine LaGrave’s What Basic Economy to Europe Will Be Like if flying Delta or American Airlines. Good tidbits to know.


If you’ve read my AIRBNB? NOT FOR ME! story, you’ll know I’m very particular when it comes to selecting a hotel, (if you haven’t read my post, take a moment – it’s pretty darn funny). Given my needs, wants and expectations, selecting a hotel can be bothersome. The first thing I look at when booking a hotel is the cancellation policy.

I try never to book the non-refundable option unless I’m positive I’m staying at that hotel. Okay, I never use the non-refundable option. I also tend to book directly with the hotel via the web site or phone reservations. I know this is a faux pas with so many hotel booking sites offering discounts, but there is a reason.

Recently, for a short trip, I used a reputable booking site (cough, Expedia, cough) because of the discounts. Paid for the reservation and received my confirmation.

Imagined my surprise when I arrived at the hotel and found there was no reservation for me. It took six attempts to reach the booking site’s customer service. Once I did, I was given a not-so-polite apology.

Apparently, the site did send my reservation, but for the wrong dates. My payment was (eventually) refunded, but not the amount I had to pay to book a room at the current rates.

That’s why I always try and book direct. Also, many hotels offer “best price matching.”

I end up getting the room at the discounted travel site price anyway, with a few extras for booking direct. These extras are even better if you’re a loyalty club member or use a special credit card like Marriott Rewards or Hilton Honors.


Once the flights and hotels are booked – I turn my attention to activities. Of course if I’m in a city for the first time, I visit the typical tourist attractions.

After that, I venture out to find Hidden Gems.  The first sites I visit are the official government tourist sites, like the one for Bath, England or this one for Tokyo. I peruse the official sites first because they provide a load of resources about various attractions in the local area.

Also, it can be reasonably assumed if  a web site for a local business is listed on the official tourism site that business (and it’s web site) is legit.

I  do peruse various sites to gather information on pricing, hours, typical crowds and special events. If it’s a popular tourist attraction like The Flavian Amphitheatre or La Tour Eiffel, I’ll mostly likely book a small group tour with fast-track entry option. Yes, it’s a bit pricey, but the time saved and lack of mental anguish is worth the price, especially if you want to visit the Catacombes de Paris, only to arrive and find the wait to be 3 to 5 hours, with no guarantee of entry. 

There are some attractions where I buy my ticket when I show up. Sometimes the price is cheaper, sometimes it’s not. Either way, if you do a little research, you’ll be prepared.

I encourage you to get out and explore like a native, and not  just visit the typical tourist attractions. You’ll no doubt find your own Hidden Gems. I can’t count how many Hidden Gems I’ve found during my travels. Each one left me with an experience I’ll never forget. It also makes for better storytelling and photo memories than the same on shot of La Tour Eiffel featured in every tourist photo since 1889.


When I vacation, I want luxury. Well, at least a reasonable facsimile of luxury. Since I’m not wealthy by any means, this means I must have a proper travel budget.

For every trip, including work-related trips, I always create a travel budget. There are many templates available, or you can create your own. Either way, having a budget helps more than it hurts. Google “How to Make a Travel Budget,” if you need help getting started.

Of course, when I begin my budget, it mostly guesstimates, but it gives me a ballpark on what the trip may cost. This way I know approximately how much too save and how long I need to save for — this requires a little more math involving average salary, date of vacation, current and future bills, etc.

When it comes to putting my money where my mouth is, my budget helps keep track of expenses, thus I have better insight on how much of my annual travel budget I’ve spent. Knowing this let’s me know if I have funds for another trip, need to save more, or if I have to adjust and plan a less expensive trip.

Having a budget is also great if you want to show friends the actual cost of a trip or use it to compare prices for Escorted Tours on various Vacation Destination sites.

There are times when the actual cost of my trip is higher than a group tour. When this happens, I must make the decision – do I give up my independence for the sake of a few dollars, or do I stay independent — do what I want, when I want? Not always an easy decision.

A budget example I did for a friend who is planning a trip to Copenhagen. All expenses are estimates.
A budget example I did for a friend who is planning a trip to Copenhagen. All expenses are estimates.


Many people can carpe diem while on vacation. If you haven’t notice, I’m not a carpe diem-type person. I must have an itinerary for my vacation. And not just any itinerary, but a very in-depth itinerary.

No, I don’t plan every moment of the day, but I do get the big things down on paper. I’ve found an itinerary helps keep me on track. It also provides very important information such as maps, phone numbers, ticket information, etc. Most importantly, it keeps me from staying in the hotel room watching television.

This is a tedious aspect to vacation planning. Good thing I’ve found a few sites to help me in this endeavor.

Visit A City is my favorite planning site at the moment. This app, which can be downloaded to your phone, lets you create a customized itinerary and book tours and activities (with Viator). Best part is it helps travelers discover must-see landmarks, historical sites, and hidden gems of in a given destination. This is very handy if you’ve never travel to a city before and aren’t sure what the city offers.

Another site is Klarna Trips. This site can draft a complete day-by-day itinerary based on your preferences. It is also customizable. It’s offers links to TripAdvisor and AirBnB, and has search options for flights, car rentals and trains.

Travefy is another option. This site at one time was free, but now it is exclusive for “travel professionals’ and “business travelers,” and not “casual travelers.”


The last aspect of my vacation preparation is to create a traveler’s checklist. Even my detailed vacation plans would be for naught  if I forgot to pack creature comforts and small necessities. Usually, it’s the obvious things I tend to forget, like glasses or Passport.

Passport - Never leave home without it. Whether traveling internationally or domestically, your passport is usually always accepted as a official government identification.
Passport – Never leave home without it!
Whether traveling internationally or domestically, your passport is usually
always accepted as an official government-issued identification document.

Therefore, my checklist isn’t just a packing list, but a detailed inventory with important tidbits, including things I need to do before I even pack and head out the door, like buying travel adapters, confirming rides to airport, making an emergency contacts list, or cleaning the house and putting the mail on hold.

Yet another daunting task. But have no fear, help is here.

Travels’ Checklist is a user-friendly site that produces a detailed, customizable and printable packing list complete with travel tips, information, and things to do before your trip.

Using a handy checklist from Travel’s Checklist, or any site that provides a handy checklist like Packtor ensures I can confidently head to my vacation destination without the nagging “I think I’m forgetting something” feeling.


That’s it. That’s my methodology for vacation planning. As you can see there isn’t a magic formula, just Good Ol’ Fashion research.

And yes, I put a lot of work into my vacations. Many have said I’m weird when they learn how much I put into my planning.

But my vacation planning has helped me traveled more than 160,000 miles, to 300 different cities and six of the seven continents. I’ve made lifelong friends and seen wonders I never thought I’d see.

Not too bad for a weirdo, huh? And I’m not done yet!

Until next time …

Have Passport, Will Travel


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s